Structural conversions of rhodamines in solution

Mchedlov‐Petrosyan, N. O.; Fedorov, L. A.; Sokolovskii, S. A.; Surov, Yu. N.; Maiorga, R. Salinas

doi:10.1007/bf00863052

Cited by 11 publications

(10 citation statements)

References 4 publications

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“…Typically, after formation of the precipitates with MB, the symmetric vibration bands of sulfonate in ABTS show a significant shift from 1124, 1032, and 656 cm –1 to 1121, 1028, and 650 cm –1 , respectively, while the N–CH 3 stretching and CN + vibration bands of MB show an obvious shift from 1178, 1141, and 1601 cm –1 to 1176, 1139, and 1600 cm –1 , respectively (Figure C). Similar phenomena were also observed for those of MG, Rh6G, and AO , (Figure S8a-c), suggesting that the encapsulation of dyes into the SIM was based on the interaction (mainly electrostatic interaction) between ABTS and the dyes. For RhB and ST, the existence of a carboxylate group in RhB and the substitute of a phenyl group in ST may weaken the electrostatic interaction with ABTS, resulting in failure in the encapsulation.…”

Section: Resultssupporting

confidence: 80%

Water-Stable, Adaptive, and Electroactive Supramolecular Ionic Material and Its Application in Biosensing

Zhang

Hao

et al. 2014

ACS Appl. Mater. Interfaces

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Developing water-stable and adaptive supramolecular materials is of great importance in various research fields. Here, we demonstrate a new kind of water-stable, adaptive, and electroactive supramolecular ionic materials (SIM) that is formed from the aqueous solutions of imidazolium-based dication and dianionic dye (i.e., 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), ABTS) through ionic self-assembly. The formed SIM not only shows good thermostability and unique optical and electrochemical properties that are raised from precursors of the SIM, but also exhibits good water-stability, salt-stability, and adaptive encapsulation properties toward some heterocyclic cationic dye molecules. UV-vis and FT-IR results demonstrate that this encapsulation property is essentially based on the electrostatic interactions between the guest dye molecules and ABTS in the SIM. The application of the SIM prepared here is illustrated by the development of a new electrochemical sensor for NADH sensing at a low potential. This study not only opens a new avenue to the preparation of the supramolecular materials, but also provides a versatile platform for electrochemical (bio)sensing.

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Section: Resultssupporting

confidence: 80%

Water-Stable, Adaptive, and Electroactive Supramolecular Ionic Material and Its Application in Biosensing

Zhang

Hao

et al. 2014

ACS Appl. Mater. Interfaces

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“…The assignment of the aromatic peaks in the range from 1620 cm ±1 to 1500 cm ±1 is supported by an investigation [35] of IR spectra of rhodamine B in the salt, zwitterionic, and lactonic form. The transition from the zwitterion or salt form to the lactone results in similar changes as observed for pyronin B before and after sublimation.…”

Section: Spectroscopymentioning

confidence: 81%

n‐Type Doping of Organic Thin Films Using Cationic Dyes

Werner¹,

Harada

et al. 2004

Adv Funct Materials

103

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We present an approach to stable n‐type doping of organic matrices using organic dopants. In order to circumvent stability limitations inherent to strong organic donors, we produce the donor from a stable precursor compound in situ. As an example, the cationic dye pyronin B chloride is studied as a dopant in a 1,4,5,8‐naphthalene tetracarboxylic dianhydride (NTCDA) matrix. Conductivities of up to 1.9 × 10–4 S cm–1 are obtained for doped NTCDA, two orders of magnitude higher than the conductivity of NTCDA doped with bis(ethylenedithio)‐tetrathiafulvalene as investigated previously, and four orders of magnitude higher than nominally undoped NTCDA films. Field‐effect measurements are used to prove n‐type conduction and to study the doping effect further. The findings are interpreted using a model of transport in disordered solids using a recently published model. Combined FTIR, UV‐vis, and mass spectroscopy investigations suggest the formation of leuco pyronin B during sublimation of pyronin B chloride.

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“…The phenomenon can be easily explained on the basis of the change of conformation of the fluorophore according to the pH. The opening of the lactam ring is catalyzed by acidic conditions, thus switching the equilibrium of the prototropic forms of the dye towards the fluorescent amide form [ 28 ].…”

Section: Resultsmentioning

confidence: 99%

New synthetic strategies for xanthene-dye-appended cyclodextrins

Darcsi¹,

Bálint²,

Benkovics³

et al. 2016

Beilstein J. Org. Chem.

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SummaryXanthene dyes can be appended to cyclodextrins via an ester or amide bridge in order to switch the fluorescence on or off. This is made possible through the formation of nonfluorescent lactones or lactams as the fluorophore can reversibly cyclize. In this context we report a green approach for the synthesis of switchable xanthene-dye-appended cyclodextrins based on the coupling agent 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM). By using 6-monoamino-β-cyclodextrin and commercially available inexpensive dyes, we prepared rhodamine- and fluorescein-appended cyclodextrins. The compounds were characterized by NMR and IR spectroscopy and MS spectrometry, their UV–vis spectra were recorded at various pH, and their purity was determined by capillary electrophoresis. Two potential models for the supramolecular assembly of the xanthene-dye-appended cyclodextrins were developed based on the set of data collected by the extensive NMR characterization.

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Structural conversions of rhodamines in solution

Cited by 11 publications

References 4 publications

Water-Stable, Adaptive, and Electroactive Supramolecular Ionic Material and Its Application in Biosensing

Water-Stable, Adaptive, and Electroactive Supramolecular Ionic Material and Its Application in Biosensing

n‐Type Doping of Organic Thin Films Using Cationic Dyes

New synthetic strategies for xanthene-dye-appended cyclodextrins

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